Roy Osing is a guy who took a startup internet company to A BILLION IN SALES! through the ‘Audacious Unheard-of Ways’ that ONLY he uses.
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Articles by Roy Osing
Forget Best Practices. Create Next Practices
Audacious Move™ of the Week Every week I share one Audacious Move™—a bold decision, hard-earned lesson, or unconventional idea drawn from decades of real-world business experience. Bold Decisions Create Extraordinary Businesses. I hope it helps you create yours. Every industry is obsessed with “Best Practices”. Study the leaders. Benchmark the competition. Copy what works. It sounds smart. It’s also the fastest way to become invisible.
Career Growth Starts With One Move Most Professionals Never Make
Bold Decisions Create Amazing Careers. I hope it helps you create yours. From Aspiration to Achievement: Create the Career Success You Deserve Everyone wants a better career. A bigger role. More responsibility. More influence. More money. But here’s the problem. Most people drift through their careers hoping someone notices them. Hope isn’t a career strategy. After spending decades leading organizations and coaching executives, I’ve learned that careers stall for three reasons: * No career plan.
The Bear Pit: The Leadership Exercise Most CEOs Are Afraid to Try
Bold Decisions Create Extraordinary Businesses. I hope it helps you create yours. Bear Pit Leadership: Turning Pressure Into Leadership Power The greatest leaders don’t hide from pressure. They step directly into it. One of the most powerful leadership practices I’ve ever used was something I called The Bear Pit—an unfiltered forum where employees could tell me exactly what they thought, with no managers, no scripts, and no fear. It wasn’t comfortable. It wasn’t predictable.
AI Isn’t Your Competitive Advantage. Using It Well Is.
Every week I share an Audacious Move™—a bold decision, hard-earned lesson, or unconventional idea to help leaders create extraordinary businesses. I hope it helps you create yours. Unlocking Business Potential: Leveraging AI for Growth In today’s rapidly evolving business landscape, artificial intelligence (AI) has emerged as a game-changing technology with the potential to revolutionize operations, boost efficiency, and drive growth across industries.
5 People Programs That Create Exceptional Customer Service
In today’s competitive business environment, exceptional customer service is a vital differentiator, and the foundation of successful service delivery rests on robust “People Programs.” These initiatives within your business plan are crucial—they shape employee behaviors and attitudes, directly impacting the customer experience. These five proven People Programs are instrumental in catalyzing a successful service strategy. Service excellence begins at the hiring stage.
5 Customer Service Moments That Turn First-Time Buyers Into Loyal Fans
Creating an Amazing Customer Moment (ACM) is essential for building customer loyalty and differentiating your brand in a competitive market. An ACM is a remarkable interaction where customers are utterly blown away by the care and service they receive. Here are five surprising ways to achieve these gasp-worthy engagements… Begin every interaction with genuine enthusiasm. A cheerful greeting conveys to customers that they are valued.
Messy Leadership: 7 Traits That Separate Great Leaders From Good Ones
Leadership is often romanticized as a polished, flawless endeavor. We imagine great leaders as composed, decisive, and always in control. But the truth is, the most impactful leaders are often the messiest. Their imperfections, struggles, and chaos are not weaknesses—they’re the very qualities that make them extraordinary. Here’s why great leaders are really messy, and why that’s your secret advantage in today’s complex world of leadership and management.
90% of Startups Fail—These 10 Moves Can Put You on a Different Path
You’ve got the idea. You’ve got the drive. You’re ready to build something great. Welcome to the thrilling—and often brutal—world of entrepreneurship. Let’s start with the hard truth: most startups fail. But that doesn’t have to be your story. After building and scaling an internet startup to billion-dollar success, I’ve learned what separates those who make it from those who don’t. It’s not just about working hard. It’s about working smart, with intention, strategy, and unwavering focus.
Not Fitting in Could Be a Sign You’re Exactly Where You Belong
In a world that often pressures us to conform, the idea of not fitting in can feel uncomfortable or even intimidating. However, not fitting in can actually be a powerful way of truly fitting in—with yourself and with the world around you. Here are three simple reasons why standing out might just be the best way to belong. When you don’t try to fit into a mold that doesn’t align with who you are, you give yourself the freedom to be authentic.
Top Talent Isn’t Looking for a Job—They’re Looking for a Reason
In today’s competitive business landscape, recruiting top talent has become increasingly challenging. With a limited pool of skilled candidates and numerous companies vying for the same individuals, the battle for talent has never been more intense. As a business leader, how can you attract and hire the people you need in this tight market?
Customers Don’t Trust Slick Salespeople Anymore
The Problem with the “Slick” Salesperson The aggressive, self-interested sales stereotype erodes trust. Behaviors like not listening, hard selling, and prioritizing the close damage long-term relationships and the profession’s image. The transformation begins by making customer loyalty the primary strategic goal. Sales must become a core strategic resource, not just a function for moving product.
Reactive Leaders Turn Chaos, Market Shifts, and Uncertainty Into Growth
The Power of Reactive Leadership: Thriving in Chaos In traditional leadership narratives, praise is often reserved for visionary strategists who anticipate trends and steer their organizations through predictable change. The archetype of a great leader is someone who can anticipate future trends with near-prophetic accuracy and navigate their organization seamlessly through anticipated changes.
Innovation Starts When You Stop Following Everyone Else
Let’s face it: following the crowd is so last decade. If everyone’s zigging, why not zag? If they’re all eating avocado toast, maybe it’s time to bring back the humble peanut butter sandwich. Like a flamingo in a flock of pigeons. Think about it: the greatest breakthroughs in history happened because someone dared to be weird. Einstein didn’t become a genius by nodding along with Newton. Nope, he said, “Hey, what if time is relative?” and bam—physics was never the same.
Leadership Edge Comes From Hunger, Not Titles or Strategy
In the world of leadership, one powerful quality separates the good from the truly great: thirst. Not for water—but for growth, for impact, and for excellence. This deep, relentless drive fuels exceptional leaders and sets them apart. They don’t just lead—they hunger for more. Great leaders are never satisfied with the status quo. They have an insatiable hunger for growth that pushes them into uncharted territory. They don’t follow—they pioneer.
Stop Delegating These 5 Critical Leadership Moves
Most conventional wisdom emphasizes delegation as a pillar of effective management. Leaders are encouraged to distance themselves from the nitty-gritty and focus on steering the ship. However, this advice can sometimes lead to a hands-off approach that neglects crucial strategic areas where leadership involvement is vital.
Leaders Who Embrace Flaws Outperform Everyone Else
The ONE THING That Makes Unbelievably Great Leaders: Being Imperfect In leadership discussions, we often hear about the need for perfection, flawless decisions, and unwavering confidence. But the truth is: truly great leaders are far from perfect. In fact, it’s their imperfections that often make them exceptional. Today, we dive into the sixth installment of our series “ONE THING To Be An Unbelievably Great Leader” — embracing ImPERFection.
Strategy Fails Without This One Leadership Skill That Turns Plans Into Results
In the mosaic of leadership qualities, there’s one skill that truly sets exceptional leaders apart: the ability to translate. No, we’re not talking about linguistic prowess, but rather the crucial capacity to transform an organization’s business strategy into actionable, meaningful directives for teams and individuals.
Leadership Edge Comes Down to One Bold Move: Disrupting Everything
There’s ONE THING that sets truly exceptional leaders apart: the ability to disrupt. Great leaders are consummate disruptors, challenging the status quo and pushing boundaries to drive innovation and growth. Why is disruption a crucial element of outstanding leadership and how can it transform organizations? Great leaders understand that disruption is not about creating chaos for its own sake.
5 Ways Exceptional Leaders Separate Themselves From Everyone Else
There’s a special breed of leaders who don’t just stand out—they redefine what leadership means. These aren’t your average leaders. They’re unbelievably great leaders with one powerful quality that sets them apart: They choose to be DIFFERENT. Here are the 5 distinct ways exceptional leaders differentiate themselves and inspire extraordinary results. Great leaders don’t waste energy trying to be “the best.” Instead, they focus on becoming The ONLY One who does what they do.
Leadership That Delivers Results Starts With Serving, Not Commanding Original
We continue exploring the essential elements of exceptional leadership, turning our attention to another critical “ONE THING” that sets remarkable leaders apart: Serving. This concept goes beyond management—it’s about leading with purpose, empathy, and impact. At its core, servant leadership flips the traditional leadership pyramid. Instead of commanding from the top, the leader supports from the foundation, empowering the team to rise and excel.
Leaders Who Simplify Win Faster, Align Teams Better, and Execute More Original
Great leadership isn’t about one magic secret—it’s about mastering many small, powerful habits. Welcome to our new 10-part series on becoming a standout leader! We’re breaking down the real, actionable habits that create exceptional leadership—one “ONE THING” at a time. The path to remarkable leadership isn’t straight. It’s organic, adaptive, and built through consistent, thoughtful actions. And it starts with Simplicity. In a world obsessed with complexity, great leaders keep it simple. Why?
Dazzle Act: Customer Experience Strategy That Turns Clients Into Advocates
In today’s unpredictable business environment, achieving sustainable growth is more challenging than ever. With fierce competition, shifting markets, and empowered customers, companies must go beyond traditional strategies to stand out. The key lies in creating extraordinary customer experiences—what I call The Dazzle Act. The Dazzle Act is a customer engagement strategy built on creating unforgettable, emotionally resonant interactions.
3 Non-Negotiable Weekly Practices That Scale Companies Past $1B
3 Weekly Priorities of an Epic Leader: Boost Performance & Growth At the core of every Epic Leader’s week is The Bear Pit—a candid, no-holds-barred meeting focused on executing the organization’s Strategic Game Plan. Unlike traditional leaders shielded by layers of management, the Epic Leader steps into this space alone, embracing vulnerability and actively seeking employee feedback. Here, listening, clarifying, and documenting insights are the leader’s main tasks.
Turn Your Big Idea Into a Crave-Worthy Business With These Three Steps
So, you’re buzzing with a new business idea. That’s fantastic! But between that initial spark and a thriving, profitable company lies a critical gap that trips up countless entrepreneurs. With stark statistics showing that 25% of new businesses fail within two years, the journey from concept to success demands more than just passion—it requires a strategic blueprint. This isn’t about complex business theory. It’s about three actionable, foundational steps that act as your launchpad.
Ghost Leadership Is Eroding Trust and Driving Top Talent Away
In today’s workplace, a troubling leadership style is on the rise—the “Ghost Leader.” These leaders are physically present but communicatively absent. They ignore emails, leave messages unanswered, and disappear when their team needs guidance most. When you share an urgent update or ask a critical question—only to be met with silence—it sends a clear message: You don’t matter. Morale drops, frustration builds, and trust erodes.
Why “Copycat Innovation” Is a Silent Leadership Trap
In the relentless pursuit of growth, many leaders fall into the trap of copycat innovation—blindly mimicking industry “best practices.” While it seems practical, this approach stifles true creativity and holds organizations back from real breakthroughs. Leaders who imitate others’ strategies often believe they’re being innovative. In reality, they’re just joining the copycat herd—adding noise, not value. True innovation requires originality, not imitation.
5 Costly Leadership Gaps That Undermine Growth and Innovation
Effective leadership isn’t just about vision and strategy—it’s also about self-awareness. Even the most capable leaders can overlook critical gaps that hinder team performance, innovation, and growth. Here are five common blind spots that leaders often ignore, along with actionable solutions to address them. Many leaders become so attached to academic models and “best practices” that they miss practical, real-world solutions. This over-reliance on theory can limit adaptability and stifle innovation.
Inspiring Followership: The Leadership Skills That Turn Vision Into Reality
Leadership isn’t just about having a title or making decisions. The true measure of a leader lies in their ability to inspire and motivate others to follow their vision. Without dedicated followers, even the most brilliant strategies remain unfulfilled dreams. So, how can you, as a leader, convince people to eagerly follow your lead and execute your organization’s Strategic Game Plan? These three essential principles will help you build unwavering buy-in and turn your vision into reality.
The Common Ways Are Failing You: 5 Unheard-of Moves That Actually Differentiate
The pressure to conform to standard “acceptable” practices and approaches is immense. In a previous post I outlined how to supplant “Common Ways” with “Unheard-of Ways”. My intent is to provide a roadmap of how to move from doing things the way everyone else does to delivering value in a unique way that no one else does. This is the second in a series to help you understand what you can do to step away from ways that everyone else exhibits and make moves that ONLY a few make.
From Dysfunction to High Performance: Three Strategies Every Team Needs
In today’s fast-paced business environment, effective teamwork is crucial for organizational success. However, many teams struggle with dysfunction, hampering their ability to contribute meaningfully to company goals. The common pitfalls that lead to team dysfunction: Misalignment with organizational goals. Internal conflicts and unclear expectations. Ego-driven leadership. Siloed thinking and lack of cross-functional collaboration. Disconnection from the company’s broader strategy.
The Thirsty Growth Leader: The Rare CEO Mindset Behind Relentless Business Growth
In the complicated and challenging landscape of business leadership, there emerges a unique breed of leader who stands out from the rest: The Thirsty Growth Leader. What sets these individuals apart is their insatiable appetite for business growth – a passion so intense that it keeps them awake at night. These leaders are constantly driven by the desire to perform at the highest level and ensure their revenues are always trending upward.
Success Isn’t About Credentials. It’s About How You Show Up
Success is a complex and often elusive concept. Two individuals with identical academic backgrounds can have vastly different career outcomes – one thriving and reaching their goals, while the other struggles to make progress. What sets these individuals apart? First and foremost, it’s crucial to understand that the number of degrees one holds is not a reliable predictor of success.
You’re Not Different Because of Your Style-You’re Different Because of What You Deliver
In today’s world, where everyone’s vying to establish their uniqueness, the concept of being different often gets chained to self-expression. People dye their hair vivid colors, adorn themselves with elaborate tattoos, or flaunt outlandish body piercings. This form of individuality reflects personal choices and preferences—it’s about expressing “the real you.” While this personal exhibit of uniqueness can be empowering, it misspends the potential of being different.
The Billion-Dollar Blueprint: 5 Proven Strategies That Turned a Startup Into a Giant
What’s the secret to a high-performing and amazingly successful company? While there isn’t a single magic ingredient, it’s the combination of many smart strategies that together create outstanding results. Here’s how we grew a startup internet company to a billion in annual revenue, highlighting five essential elements in achieving unmatched performance. 1. A Flexible Plan — We adopted a strategy that was “just about right” rather than perfect.
Want Customer Delight? Start by Rewriting These 3 Internal Rules
In today’s business world, fostering customer delight is not just a strategic advantage; it’s a fundamental necessity. A key component in achieving this is through the careful crafting of internal rules and policies. These are not merely procedural or bureaucratic necessities; rather, they are vital instruments that can either enhance or hinder the customer engagement process. When approached thoughtfully, company policies can significantly contribute to building lasting customer loyalty.
Want Customer Delight? Start by Rewriting These 3 Internal Rules
In today’s business world, fostering customer delight is not just a strategic advantage; it’s a fundamental necessity. A key component in achieving this is through the careful crafting of internal rules and policies. These are not merely procedural or bureaucratic necessities; rather, they are vital instruments that can either enhance or hinder the customer engagement process. When approached thoughtfully, company policies can significantly contribute to building lasting customer loyalty.
The Only 3 Things That Truly Win Customers - And Most Companies Get Them Wrong
In the competitive landscape of modern business, a pivotal question looms large over organizations: “Why should I do business with you and not your competitors?” Surprisingly, many companies overlook this crucial inquiry, often opting for generic and empty CLAPTRAP slogans like “We are the best” or “We are number one.” Such clichés tend to ring hollow, leaving potential customers skeptical and disengaged. #1.
The Only 3 Things That Truly Win Customers - And Most Companies Get Them Wrong
In the competitive landscape of modern business, a pivotal question looms large over organizations: “Why should I do business with you and not your competitors?” Surprisingly, many companies overlook this crucial inquiry, often opting for generic and empty CLAPTRAP slogans like “We are the best” or “We are number one.” Such clichés tend to ring hollow, leaving potential customers skeptical and disengaged. #1.
Planning Dependence: The Silent Strategy Killer in Modern Leadership
In the business world, achieving a successful strategy is often viewed as the gold standard for leadership. However, many leaders fall into the trap of Planning Dependence, a state where excessive focus on traditional, rigorous planning models hinders practical implementation. In the pursuit of creating a “perfect” plan, leaders often overlook the dynamic and unpredictable nature of the real world, thereby limiting their strategy’s effectiveness.
Planning Dependence: The Silent Strategy Killer in Modern Leadership
In the business world, achieving a successful strategy is often viewed as the gold standard for leadership. However, many leaders fall into the trap of Planning Dependence, a state where excessive focus on traditional, rigorous planning models hinders practical implementation. In the pursuit of creating a “perfect” plan, leaders often overlook the dynamic and unpredictable nature of the real world, thereby limiting their strategy’s effectiveness.
Are You Suffering From Textbook Infatuation? The Hidden Trap Holding Leaders Back
In today’s fast-paced and ever-evolving work environment, effective leadership is more crucial than ever. However, many leaders find themselves ensnared by the constraints of textbook solutions. This phenomenon, which I call “Textbook Infatuation” occurs when leaders become overly reliant on academic theories and frameworks instead of considering the practical realities of their teams and organizations.
Are You Delegating or Disconnecting? The Subtle Trap Even Great Leaders Fall Into
Modern leadership principles emphasize the importance of delegation. Leaders are encouraged to empower their employees, trust them to execute their roles, and avoid the supposed pitfalls of micromanagement. However, this trend can lead to a counterproductive phenomenon that I call known as “Overindulgent Delegation”. While the intention behind empowering employees is sound, an overreliance on delegation can result in critical organizational activities being neglected.
Beyond the Résumé: Why Caring Is the Most Overlooked Hiring Advantage
In today’s dynamic business environment, effective leadership extends beyond strategy development; it hinges on the quality of recruitment. However, many leaders adopt a “hands off” hiring approach, assuming that delegating recruitment to a Human Resource function is sufficient. This mindset often overlooks the critical aspects that transform a good hire into an exceptional one. Traditional HR practices tend to focus on quantifiable metrics such as technical skills and previous experience.
Inside the Bell Curve: 10 Reasons People Choose the Crowd Over Greatness
The well known Bell Curve is an excellent expression of today’s social dynamics. Like this curve, which bulges in the middle around the Y-axis populated by the masses, and tapers off into less dense tails, society, too, has its ‘crowds’ and ‘outliers’. Within this humdrum middle zone, the multitude find comfort, security, and identity, gravitating naturally to the “blobbed” center without much introspection. But why do people land in the crowd, and more importantly, why do they choose to stay? #1.
Want Faster Business Growth? Start by Saying No to These 3 Things
In business, growth isn’t just a goal—it’s a necessity. Achieving it, however, requires precision, focus, and sometimes, bold leaps into the unknown. As traditional five-year plans become relics in our rapidly evolving economy, adopting a more targeted approach is crucial for businesses seeking to accelerate their growth. Here’s how you can strategically position yourself for success over the next 24 months. Start by setting a courageous revenue target for the next two years.
To Stand Out, You Must Opt Out: Escaping the Trap of Average Original
In today’s warp-speed world, being average means blending seamlessly with the majority. It suggests a state of comfort, where one feels secure and unnoticed, navigating life in a predictable manner. Average people tend to achieve average results, reflecting a life that is stable but not extraordinary. While there is a sense of warmth and safety in being average, the pressing demand for innovation and adaptability in our uncertain world beckons a departure from this norm.
ME Marketing: How to Build a Personal Brand That No One Can Compete With
In today’s digital age, personal branding has become more crucial than ever. Whether you’re a freelancer, entrepreneur, or professional, effectively marketing yourself can be the key to standing out in a crowded marketplace. This is where “Me Marketing” comes into play – the strategic promotion of oneself to build an unmatched strong personal brand. #1. Define Your Unique Brand Identity — Start by identifying what sets you apart from others.
ME Marketing: How to Build a Personal Brand That No One Can Compete With
In today’s digital age, personal branding has become more crucial than ever. Whether you’re a freelancer, entrepreneur, or professional, effectively marketing yourself can be the key to standing out in a crowded marketplace. This is where “Me Marketing” comes into play – the strategic promotion of oneself to build an unmatched strong personal brand. #1. Define Your Unique Brand Identity — Start by identifying what sets you apart from others.
They Wanted Us To Fail - These 5 Moves Built a Billion-Dollar Business Instead
My life as a leader was never easy. We took an early stage internet company to a BILLION IN SALES in a monopoly telephone organization. We had to create a different culture. We have to shed the ways of the past and cut a new audacious path. To say there were obstacles that we had to confront would be a gross understatement. Some of my executive peers wanted us to fail. A new team was necessary with new skills and competencies. It was painful. But it was worth it. #1.
The Only Strategy That Makes Your Brand Truly Irreplaceable
In today’s business world, branding strategies typically adhere to a structured set of guidelines. These include identifying a market problem, developing a suitable solution, branding that solution, and communicating the brand to the intended audience. This approach, while useful in maintaining a customer-focused and solution-oriented outlook, misses a vital element: uniqueness. What’s Missing in Current Branding Strategies?
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